Manufacture of acid dyestuffs of the phenonaphthosafranine series and the products



The resulting' phenonaphthosafranine sulphonic acids are characterized by the ortho (16) positionrof one 'sulpho-group tothe safranilej-nitrogen, vwhich has the ,efeet *in general of improving the 'soiubility vandthe .fastness to 1139i ly owing' to this -16-sulpho-group the dyev. stuffs are fast to alkali. v

li'llea'dyestuis V.obtained laccording tol this `pt fzess are soluble in Water and insulphuric aci f Y f V process `ofl manufacturev v could" not be foreseen, since'n'oV similar kind of cond'eiisa-y tion ,vyith Aorthoaminoaryl-sulphonic acids has been eect upon the reactions possessed by lstrong acid radicals in ortho-position to therk aminooup did not allow oa prospect 'of success. hen derivatives of para-phenylene-diam ine are used blue to blue-*greeny dye'studs of outstanding clearness (yf-tint and pronounced fastness especially to alkali and light'are obtained. l ,i n Y The isorosinduline-G-sulphonic acids used as parent materials kcan be made from the sulphonic acids of the 'neutraly bluc series by treatmentwith sulphites in accordance with U. S; patents eciication No. 6 7,703 and subsequent oXi ation. Positions 4 and 8 to The following example illustratesthefin-K- boiling and the solution is mixed with the concentrated` aqueous solution of 24.5 parte, s 55 0f Vdiethyl-para-phenylenediamine sulphonic; myacid (obtainedfrom para-nitrochlorobenzenef sulphonic acid diethylamine andsiibse-- quent reduction) in the forno of its sodium salt. 55 partsof acetic acid of 8O per cent. i y

lstrength are added to the 'solution and then at the boiling 'temperature of the alcohol there are dropped'in during the course of about 45 minutes a highly concentrated soy lutionrof 31' parts yoi sodium bichrom'ate-g-r JfWater is now added and if necessary a porfulling as Well as a marked shift; the tnts-towardgreenf-blue, i Especial-V soluble blue green diet discovered and the kiiownhindering y 15 may containalkyl-,valkyloXy-, hydroXy-,v acidylamino-groups andha loi ina c fairy.

tion of the alcohol is distilled; the diethylisorosinduline-monosulhonic acid which separates in fvorm of nee les Qf`c9ppery apiawshd flee .frrf lsalilm by meais di dvater'. `In` concentrated' acetic acid .nonnlfaa al'. :i ..1,..-. y: '1-2.' -xil i, f .H a. z i The dyestu is converted into the easily h lisorosinduline2:6 f-diupliniaefdb 156i i'vlish 50'1 commcial bisulp ite solution an subseesquent ogidetgn ,of ,theA soluble leuoofcouk, meandofiaii-Ljlt; 'es woolgre luejnuddyetintsand"dsso ves in concensfi. Selphilrclaaeflw ahreazeivielet @b1- sulphoniofcid) i ichhaseen previously: treated'v with somewhat more, than the theoretizlil lpro ortionof sodium: carbonate v4to proa dyestui showing a grass-green reaction with sulphuric yacid and dyeing animal fibre in a sulphuric acid bath pure, blue tints of remarkable fastness to light and alkali. What I claim is 1 l. A process vfor the manufacture of equalizing acid dyestuli's of the Vphenonaphthosafranine series fast to alkali; consisting in condensing an unsymmetrical Nalky1para v phenylenediamine derivative 'having a sulpho-group in ortho position to the primary amino-group according to the general formula:

i NH:

N som R/ \Rl i A, with anisorosinduline sulphonic acid having `"'asulpho-group in position 2 and another in 50. y i. e position 6, yaccording to the general formula: parts of phenyl--naphthylamine are disi f solvedv in 250 parts of ethyllalcohol While?! where R and R1 represent hydrogen or alkyl thedyestuif dissolves to a green blue solu-YK blyy alkaline solution; The-bronze crystalline powder obtained by salting but isf,

phoniecidfrnad kijf-'reduction of 'f lineazomonometh bortliaf toltidine-l nieta-f ige Y `"and yY representsl `a {sulpho -or acetamido n group.

- amino-group `,according to Ythegeneral forn asulpho group 405 safranine series obtained by condensingan;

` having a wf y i V- where RandiR1 represent hydrogengor alkyl,

, 2.. Aiprocessforthenlanufacturefof equal,- izing yacid dyestui'saof the phenonaphthosafranine `serifes fast to alkali,V Consisting in ,condensing an un'symmetricalNialkylfpara# v Y yphenylenediamine derivative havingy a` sulho-group in ortho position'tofthe primary to `the general Aformula where Rand R1 represent hydrogensor alkyl t I .and Y1 relilresents a lsulphogor'acetarrn'do'y A *n group: Y w f i 3. new -articles of manufacture the here# in described dyestus of the phenonaphthoisorosincluline sulphonic acid having at least two sulpho-gr'oupsV with an unsymmetrical N -alkylfisulpho-group. in ortho-position ito theprima a 'and Y represents arsulpho or racetamido 'n group, saiddyestuffsvc'onstitutin darklpow-r 1n water withy red ishy blueto ders soluble' I yieldingon the animal br para phenylenediamine derivative kY amino g1"-011p,}and constituted ac-r f j 'i cordingfto the formula; y y

yblue tints 'faet to alkali and light. y Inwitnese whereof I have hereunto my namefthis 21st dayof'Juxief1928.*y

signed.

phuriclacid withaV greento violet color esblue togreensh.` Y

'zo` .55 e n 1 BAULLAEUGER. i,

with an isorosinduline-eulphonic,acid having] v 1n position 2,41another 1n posi-yv Y v .f tion 6 anda third;1nany'position,accordlngl greenish bluefcoloration', dissolving` in*` su1- 'i 

